Dempsey fights the best version of Williams. The best Williams was better than Firpo and had at least as much power. On the other hand, Dempsey had punching power somewhere between Bob Satterfield and Sonny Liston and they both could be fast and explosive. Williams at 6'3 210-215 would be the bigger man compared to Dempsey's 6'0 187-190.
I went with Dempsey here. I know Cleveland is the bigger guy and hits pretty damn hard himself . But his chin and defense were questionable. I think jacks ballistic punching style might get to him before Williams can really get going. Not guaranteed of course but that’s just how it looks to me on the surface.
I'll go with the bigger guy who had alot of power along with good coordination and quickness. Williams stop him.
